Fragmentation of nitrone triflates to 9-membered rings

John A. Murphy, Mohan Mahesh, Gary McPheators, R. Vijaya Anand, Thomas M. McGuire, Robert Carling, Alan R. Kennedy

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

Original languageEnglish
Pages (from-to)3233-3236
Number of pages4
JournalOrganic Letters
Volume9
Issue number17
DOIs
Publication statusPublished - 16 Aug 2007

Keywords

  • nitrone triflates
  • cyclization
  • amides

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  • Equipment

    x-ray diffractometer

    Alan Kennedy (Manager)

    Pure And Applied Chemistry

    Facility/equipment: Equipment

  • Cite this

    Murphy, J. A., Mahesh, M., McPheators, G., Anand, R. V., McGuire, T. M., Carling, R., & Kennedy, A. R. (2007). Fragmentation of nitrone triflates to 9-membered rings. Organic Letters, 9(17), 3233-3236. https://doi.org/10.1021/ol071049d